Celecoxib

Celecoxib
Skeletal formula of celecoxib
Space-filling model of the celecoxib molecule
Clinical data
Pronunciation/sɛlɪˈkɒksɪb/ SEL-i-KOK-sib
Trade namesCelebrex, Onsenal, Elyxyb, others
AHFS/Drugs.comMonograph
MedlinePlusa699022
License data
Pregnancy
category
Routes of
administration		By mouth
Drug classCyclooxygenase-2 (COX-2) inhibitor
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityUnknown[6]
Protein binding97% (mainly to serum albumin)[6]
MetabolismLiver (mainly CYP2C9)[6]
Elimination half-life7.8 hours; 11 hours (mild hepatic impairment); 13 hours (moderate-severe hepatic impairment)[6]
ExcretionFaeces (57%), urine (27%)[6]
Identifiers
  • 4-[5-(4-Methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.211.644 Edit this at Wikidata
Chemical and physical data
FormulaC17H14F3N3O2S
Molar mass381.37 g·mol−1
3D model (JSmol)
  • c1cc(C)ccc1c2cc(C(F)(F)F)nn2c3ccc(cc3)S(=O)(=O)N
  • InChI=1S/C17H14F3N3O2S/c1-11-2-4-12(5-3-11)15-10-16(17(18,19)20)22-23(15)13-6-8-14(9-7-13)26(21,24)25/h2-10H,1H3,(H2,21,24,25) checkY
  • Key:RZEKVGVHFLEQIL-UHFFFAOYSA-N checkY
  (verify)

Celecoxib, sold under the brand name Celebrex among others, is a COX-2 inhibitor and nonsteroidal anti-inflammatory drug (NSAID).[7] It is used to treat the pain and inflammation in osteoarthritis, acute pain in adults, rheumatoid arthritis, psoriatic arthritis, ankylosing spondylitis, painful menstruation, and juvenile rheumatoid arthritis.[7] It may also be used to decrease the risk of colorectal adenomas in people with familial adenomatous polyposis.[7] It is taken by mouth.[7] Benefits are typically seen within an hour.[7]

Common side effects include abdominal pain, nausea, and diarrhea.[7] Serious side effects may include heart attacks, strokes, gastrointestinal perforation, gastrointestinal bleeding, kidney failure, and anaphylaxis.[8][7] Use is not recommended in people at high risk for heart disease.[9][10] The risks are similar to other NSAIDs, such as ibuprofen and naproxen.[11] Use in the later part of pregnancy or during breastfeeding is not recommended.[7][1]

Celecoxib was patented in 1993 and came into medical use in 1999.[12] It is available as a generic medication.[13] In 2022, it was the 93rd most commonly prescribed medication in the United States, with more than 7 million prescriptions.[14][15]

  1. ^ a b "Celecoxib (Celebrex) Use During Pregnancy". Drugs.com. 4 May 2020. Archived from the original on 25 January 2021. Retrieved 5 May 2020.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  4. ^ "Celebrex 100mg capsule - Summary of Product Characteristics (SmPC)". (emc). 13 January 2020. Archived from the original on 6 August 2020. Retrieved 5 May 2020.
  5. ^ Cite error: The named reference Celebrex FDA label was invoked but never defined (see the help page).
  6. ^ a b c d e McCormack PL (December 2011). "Celecoxib: a review of its use for symptomatic relief in the treatment of Osteoarthritis, Rheumatoid Arthritis, Psoriatic Arthritis and Ankylosing Spondylitis". Drugs. 71 (18): 2457–89. doi:10.2165/11208240-000000000-00000. PMID 22141388. S2CID 71357689.
  7. ^ a b c d e f g h "Celecoxib Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. 11 November 2019. Archived from the original on 20 May 2019. Retrieved 5 May 2020.
  8. ^ Cite error: The named reference Coxib2013 was invoked but never defined (see the help page).
  9. ^ Antman EM, Bennett JS, Daugherty A, Furberg C, Roberts H, Taubert KA (March 2007). "Use of nonsteroidal antiinflammatory drugs: an update for clinicians: a scientific statement from the American Heart Association". Circulation. 115 (12): 1634–42. doi:10.1161/circulationaha.106.181424. PMID 17325246.
  10. ^ "Should you still take Celebrex?". Consumer Reports. August 2009. Archived from the original on 18 December 2015. Retrieved 27 December 2015.
  11. ^ Stein R (25 April 2018). "FDA Panel Affirms Safety Of Painkiller Celebrex". NPR. Archived from the original on 20 May 2018. Retrieved 19 May 2018.
  12. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 522. ISBN 9783527607495. Archived from the original on 27 April 2021. Retrieved 13 October 2020.
  13. ^ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 1097–1098. ISBN 9780857113382.
  14. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  15. ^ "Celecoxib Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.